It's a great idea to start back slow, and to date lightly to see what happens. If anything, this should help her to overcome any insecurities and sense of pressure that she may feel.
In terms of your OW, what an interesting story. It always amazes me to hear what folks go through. I think DBing is amazing in that it helps to strip away the WAS as a distraction for one's own work/development. I doubt she and her XW had enough time/space to truly work on themselves. Maybe that explains the repeated failures.
Tread carefully with your heart, my friend.
Know that I'm rooting for you and I truly hope you don't have to join me in Surviving.
